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Single in Chicago

Roof, the aptly named rooftop bar at theWit hotel, has a scene and a view.Credit
Daniel Borris for The New York Times

IT’S hard to decide, while sipping a citrine cocktail called Sex on the Roof, what to gawk at first: the go-go dancers in crimson panties or the tallest building in the Western Hemisphere, Willis Tower, soaring like a giant glass beanstalk just beyond the windows. Either way, at Roof, the glossy club atop theWit hotel in Chicago, if you’re single you can’t lose: should a stranger fail to take your breath away, the skyline will.

As an architect’s daughter (one who built a foam core replica of a Frank Lloyd Wright house when she was 12), I’d long wanted to visit Chicago, where Wright buildings are practically as common as pizza joints. As a veteran solo traveler not content to turn in early, a spate of posh new boîtes was a bonus.

Of course, parachuting into a major city on one’s own has its perils. It’s not like lolling on a beach or rafting through the Grand Canyon. In a city, there are dodgy neighborhoods, dodgier men and jammed bars and restaurants where you’ll be parked at a table for one. Chicago, though, is hardly as high-voltage as Tokyo or New York, even though it still has the big-city qualities solo travelers crave: culture, night life and a mass transit system to explore it all. It even has white sandy beaches beneath all those skyscrapers. Indeed, friends had described Chicago as a more leisurely and hospitable New York, a city where getting into some hot spots is a breeze compared with lining up outside clubs in Manhattan’s meatpacking district.

Not that I don’t love my hometown. But a little more hospitality wouldn’t hurt. Having spent the winter slogging through a dizzying calendar, it was time for a change of pace. I packed a bag and grabbed my iPod, already loaded with Frank Sinatra. Chicago was calling.

Swoosh! They opened a door and I was inside theWit, instantly warmer but taken aback by the man perched on a tiny balcony high above my head, strumming a guitar like a folk-rock angel. This nearly 300-room Doubletree by Hilton, with a lightning bolt zigzagging across its exterior and jam sessions in the lobby, sure doesn’t feel like a Doubletree.

Opened in 2009, theWit bills itself as a splashy party stop amid the downtown bustle — advertisements for Roof show women in bikinis and stilettos, and bare-chested men brandishing Super Soaker water guns — precisely the kind of place I typically avoid. But my curiosity about this much-ballyhooed club won out. And you can’t beat the location. Sure, I could have stayed in the tony Gold Coast amid lavish town houses, or in artsy Wicker Park with its laid-back bars, or in another of the city’s dozens of neighborhoods. But since this was my first visit I chose the Loop, a constellation of theater, night life and shopping in the heart of Chicago, near Millennium Park, the Art Institute and public transportation.

It’s here, at the State and Lake Street rail station, that you’ll find theWit. At the front desk the staff was so friendly I suspected they were overcompensating for some unpleasant news they were about to spring. But all I got was a warm cookie and a key. Even later, when I gravely pointed out that I had been charged for the minibar “intimacy kit,” which I did not use (really), the fee was removed with a smile. The geniality was almost unnerving.

My king room, reasonably priced for downtown Chicago at $229 a night, was airy and modern, with a bird’s-eye view of the nearly six-story vertical C-H-I-C-A-G-O Theater marquee. Speaking of birds, I feared that one was trapped in the hallway, but it turns out that chirping is piped in through speakers. I swear I also heard frogs. Or crickets. It was oddly soothing, like the iPad app I use for insomnia. While such touches are fun, I was there for convenience, including easy access to Roof — my first stop.

There on the 27th floor was a smattering of casually dressed couples and klatches of friends. No half-naked women. Yet.

I took a seat. Panoramic views from the deck and floor-to-ceiling windows made it easy to be simultaneously present and miles away. Gazing out at Marina City’s towers, rising like two corncobs (as the locals call them) from the banks of the Chicago River, I daydreamed about what it might be like to live there. Had I peered through the telescope, I might have lingered even longer, zooming in on one real estate fantasy after another.

Photo

RockIt Bar & Grill on Hubbard Street.Credit
Daniel Borris for The New York Times

On a different evening at Roof, this time well past midnight, two go-go dancers twirled like woozy tops, flanking a D.J. who was blasting Paula Abdul’s “Straight Up.” It was more lively than the night I arrived, which suits the space: it’s too sprawling for tête-à-têtes. Still, I later wondered aloud to a man I met why a lounge with fire pits, a 12-foot-wide HDTV monitor, and million-dollar views felt it also needed to throw in a couple of dancers in panties.

JUST because you travel to a city on your own doesn’t mean you have to explore it on your own. One often overlooked way to connect with other solo travelers is to join a MeetUp group. For the uninitiated, MeetUp is a Web site through which people with shared interests can participate in free local activity groups all over the world. During a recent week in Chicago, there were more than 1,400 MeetUps, including ones offering happy hours, beach volleyball and live jazz. If I could have squeezed it into my itinerary, I would have attended a Windy City Explorers MeetUp, which organizes visits to different neighborhoods and historical sites. Or I might have tried 312 After Hours Nightlife Social Scene, whose coming events include an after-work party at a W hotel, an art walk and a wine tasting. Another popular MeetUp, MingleAround, is specifically for singles.

Offline, Chicago goes the extra mile to help tourists get their bearings (something Los Angeles and other sweeping cities would greatly benefit from doing). The Chicago Greeter service, for instance, provides free personalized tours of a neighborhood or special interest (food, African-American heritage, gay-friendly areas), but, sadly for me, requires reservations at least 10 days in advance. So I thought I’d try the next best thing: An InstaGreeter, the Ramen Noodles of tour guides. Local volunteers, they lead free hourlong walks, no reservations required.

Unfortunately, I arrived at the Chicago Cultural Center’s Visitor Information Center, home of the InstaGreeter, to discover that he or she was out on another tour. Luckily, exploring Chicago on your own is not like wandering around Turks & Caicos, my previous solo adventure: no one looks at you sideways when you dine alone, and there’s more to do than stick a straw in a coconut and work on your tan.

And so I decided to improvise my own walking tour of nearby Millennium Park, once a mess of railroad tracks and, since 2004, more than two dozen acres of postmodern architecture.

I marveled at the ribbons of stainless steel that twist into Frank Gehry’s Jay Pritzker Pavilion and paused before Cloud Gate, the shining 110-ton, kidney-shaped sculpture by Anish Kapoor that reflects the skyline and amazes passers-by as it multiplies and distorts their reflections. From the Great Lawn, I crossed Renzo Piano’s spare, steel Nichols Bridgeway over the Lurie Garden and Monroe Street, and disappeared into the Art Institute of Chicago. If you’re not careful the hours will disappear too as you meander from one major work to the next, be it “American Gothic” by Grant Wood or “Mao” by Andy Warhol.

Yet another way to put the city in context is to see it by boat, bus or bike. I opted for the Chicago Line Cruises architectural tour of more than 50 skyscrapers dotting the Chicago River, which everyone told me is a must.

I boarded the boat almost dead last and decidedly annoyed: there weren’t enough good seats or cookies (get there early if you want either). For an hour and a half I sat shivering as we glided through history, from the Great Chicago Fire of 1871 to the city’s postwar revival and beyond.

As the sun set, our guide spoke of how the 82-story Aqua Tower is the tallest building in the world designed by a woman; how employees of the Montgomery Ward Building (more than a million square feet) used to wear roller skates to fill orders; how the former Main Chicago Post Office (once the largest in the world) masqueraded as Gotham City Bank in the 2008 Batman film, “The Dark Knight.” I craned my neck upward. “Density,” said our guide, pointing up at the skyline shimmering in the dying sun, “creates vitality.”

I shivered. This time, it wasn’t because I was chilly. It was because the Windy City blew me away.

Once you check off some tourist sites, you can zero in on more under-the-radar attractions. Take, for instance, Wicker Park. Out of the shadow of skyscrapers, this is one of the neighborhoods that make Chicago a more breathable city than New York. Town houses abut thrift shops and unusual boutiques. If chakra crystals are your thing, stop by Ruby Room, a spa, salon and inn, to measure your electromagnetic field or attend a meditation class ($17), which a saleswoman said would be led by a former N.F.L. player. As I walked North Milwaukee Avenue, a chalkboard outside the Filter Cafe hyped the Vegan Slut: a lumpy coffee, banana, coconut, chocolate syrup concoction that I never want to swallow again. But that’s not the point. Inside, single people can be alone together, in the best of ways.

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Oak Street Beach.Credit
Daniel Borris for The New York Times

A vast, unhurried joint, Filter is part coffee house, part used-furniture showroom, thanks to a jumble of coffee tables and sofas. People in their 20s and 30s adorned with clunky 1980s-style headphones and glasses were reading and eating alone on couches, or clacking on their Macs.

You could spend a whole weekend in places like Wicker Park and Bucktown with their neighborhood bars and denim-and-flannel dress code. The city’s newer, more plush spots require a party dress and guts, as I would soon find out.

After thumbing through the The Chicago Reader, I headed for the door, which a man on his way in stopped to hold. I thanked him and a curious thing happened: he didn’t grunt or mumble “Welcome.” Instead, he looked at me and said, “It’s a pleasure.”

Back outside, as I struggled to walk against a strong wind, a stranger driving through an intersection slowed down and shouted out the window that I’d find a cab line around the corner. I waved appreciatively.

That’s my kind of town.

IT was Saturday night and I was readying myself for barhopping, which is not as simple as it sounds. In New York, the subway goes practically everywhere. In Miami Beach, you can walk. Chicago, though, requires some planning. The bar scene is not concentrated, and there are endless places to go: dives, blues joints with live music, chic nightclubs, hotel bars. Mind you, if you heed the advice of locals you will skip Rush and Division Streets, an area they describe as a meat market and tourist trap. The surrounding blocks are renowned for men of a certain age and the gold-diggers who love them. As one man I met put it: “They call that place the Viagra Triangle.”

So where to go?

I asked bartenders, waiters, residents, hotel staff members. Many names were uttered. But one place came up more often than any other: the Pump Room at the Public. The hotel, which opened last year in the Gold Coast neighborhood after a redesign by Ian Schrager, was formerly the Ambassador East of Hitchcock’s “North by Northwest” fame.

There was the matter of getting there, however. Equipped with a Google map of every bar I hoped to visit, I planned to walk everywhere. Yet I was foiled again and again like a video game avatar, either because there was no train stop or because I couldn’t decipher my map. I ended up hailing a cab to the Pump Room, but if I hadn’t, I could have texted for one. You read that correctly. The previous night I had texted my location to 777222 (you can also download an app at GoFastCab.com) and instantly received a reply confirming that a car was on its way. That’s a game changer for solo travelers because it means never having to roam the streets in the wee hours searching for a ride. When a yellow cab rolled up, it felt as magical as a prince galloping in on a white horse.

But back to the Public hotel, where, outside, women were teetering in stilettos — tipsy, smoking, gabbing on cellphones, or all of the above. Had I been teleported to the meatpacking district? I entered the lobby. On one side is the Pump Room, an ivory supper club with softly glowing orbs above a sea of tables, including Booth One and a phone from bygone days of Hollywood V.I.P.’s — Marilyn Monroe, Judy Garland, Clark Gable — who are now but ghosts. Places like this, elegant as they are, can be awkward if you’re on your own.

Then again, so can places like RockIt Bar & Grill on Hubbard Street, a popular place to bar crawl. After being carded (Cheers, Mr. Bouncer), I headed upstairs where, beneath deer antler chandeliers, throngs of young people were fist-pumping to disco remakes of “The Wall” by Pink Floyd and “Edge of Seventeen” by Stevie Nicks. I stood near the bar, trying not to look uncomfortable. Smiling at a circle of “X-Files” Lone Gunman-types, I inched past them and down some stairs. Unable to get my footing, I inadvertently grabbed not the railing but the thigh of a man sitting on it. He smiled and said something I couldn’t hear. In this town, some people are so affable you don’t know if they’re flirting or simply being polite. What I do know is that once you start squeezing strangers, intentionally or not, it’s time to go.

After sampling bar after bar with Goldilocks-like resoluteness, I eventually found one that felt just right: Pops for Champagne, a sleek, upscale lounge with a roundish bar and some 200 bubbly selections. Footage of spring fashion shows — Derek Lam, Luca Luca, BCBG — silently streamed across screens above fetching bartenders. European lounge music was wafting from the speakers as smartly dressed men and women laughed beneath dim (read: flattering) lights.

As I slid onto a stool, from which I would order a glass of Gosset Grand Blanc de Blanc, a dark-haired stranger turned to me.

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At Roof.Credit
Daniel Borris for The New York Times

“I love your dress,” he said.

Was it a come-on? Or just another friendly comment?

In Chicago, you never know.

SECOND CITY, SOLO

The Good

Hospitality The Chicago Office of Tourism and Culture offers audio tours of Millennium Park featuring Frank Gehry, Anish Kapoor and others (download it at downloadchicagotours.com) as well as custom walking tours (chicagogreeter.com), all free.

Weather Most of the year, Chicago lives up to its Windy City moniker, making it difficult to enjoy its al fresco and architectural charms. In late summer, it can be blistering hot — upward of 100 degrees.

Empty Streets Few avenues are bustling late at night. Take care: Homicides and shootings have increased over the last year.

Cost New high-end hotels and bars mean higher prices.

Transportation The rail system is great, but it’s not as far-reaching as those in some other cities. You’ll have to supplement it with buses and cabs.

BELLY UP

In Chicago, there’s a bar for every palate. Here’s how to find one that’s right for you.

For the Cubs Founded in the 1930s as Ernie’s Bleachers, a hot dog stand hawking beer by the pail, Murphy’s Bleachers is now a perpetually packed sports bar across the street from — what else? — the bleachers at Wrigley Field. Never mind that the Cubs haven’t won a World Series since 1908. You can enjoy beers with the throngs who love them anyway. 3655 North Sheffield Street; (773) 281-5356; murphysBleachers.com.

For the Boys In Boystown, where you can easily find a place to sing show tunes, dance (Sidetrack is a classic) or screen “RuPaul’s Drag Race,” the newcomer Elixir is a more mellow spot to kick back and sip a specialty cocktail. 3452 North Halstead Street; elixirchicago.com.

For the ElitistsIf you thinkyou can just saunter up to the bar at the Aviary,think again. A limited number of reservations are accepted each day for seatings at 6, 8 and 10 p.m. Would-be patrons must e-mail their requests to reservations@theaviary.com. If selected, you will be contacted by 4 p.m. the day of the reservation. So much for advance planning. 955 West Fulton Market; theaviary.com.

For Those Who Want to Sing the Blues Whether you want a gospel brunch or a late-night jam fest, it’s worth checking the schedule at House of Blues Chicago, which has featured artists like the Who and Al Green. 329 North Dearborn Street; (312) 923-2000; houseofblues.com.

Correction: July 22, 2012

A map on July 8 with the cover article about exploring Chicago as a single traveler located incorrectly the Montgomery Ward Building where employees used to wear roller skates to fill orders. It is on the Chicago River, not near Lake Michigan. A corrected map can be found at nytimes.com/travel.

STEPHANIE ROSENBLOOM is a reporter for the Travel section. This is the second in a series of articles about traveling alone.